ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside | 162600-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
• 英文别名: Ethyl 3,4,6-tri-O-benzyl-1-thio-beta-D-galactopyranoside；(2S,3R,4R,5S,6R)-2-ethylsulfanyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 162600-08-0
• 化学式: C₂₉H₃₄O₅S
• 分子量: 494.652
• InChiKey: NTZPSRLDRFUPBG-RQKPWJHBSA-N

物化性质

• 沸点：
  640.5±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 4-二甲氨基吡啶 、 氢氧化钾 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 三乙胺 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 34.5h， 生成 methyl (3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)-(allyl 3,4-di-O-methoxymethyl-β-D-glucopyranosid)uronate
  参考文献：
  名称：

  Synthesis of the trisaccharide portion of soyasaponin βg: evaluation of a new glucuronic acid acceptor

  摘要：

  The synthesis of the trisaccharide portion of soyasaponin betag was successfully achieved using a new glucuronic acid acceptor: methyl 1-O-allyl-3 4-di-O-methoxymethyl-beta-D-glucuronate (9). This compound and methyl 1-O-allyl-3,4-di-O-tert-butyldimethyl-silyl-beta-D-glucuronate (8) were both prepared from glucuronolactone via a glycal intermediate. The former compound 9 was successfully coupled to ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-beta-D-galactopyranoside (13) in excellent yield. Synthesis of the protected trisaccharide was then completed by the addition of a suitably protected rhamnose derivative to the disaccharide portion. The reactivity of the glucuronic acid derivative 9 was also explored with trichloroacetimidate and fluoride donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00195-2
• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 在 二甲基二环氧乙烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 生成 ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Conversion of d-Glucals into l-Glycals and Mirror-Image Carbohydrates

  摘要：

  L-Glycals can be prepared in seven steps from readily available D-glucals, enabling the facile construction of mirror-image carbohydrates such as the L-lactosamine derivative shown above.

  DOI：

  10.1021/ol036183m

文献信息

• Formation of 1,1-α,α-Glycosidic Bonds By Intramolecular Aglycone Delivery. A Convergent Synthesis of Trehalose
  作者：Matthew R. Pratt、Clifton D. Leigh、Carolyn R. Bertozzi

  DOI：10.1021/ol034836t

  日期：2003.9.1

  [GRAPHICS]We report a new synthesis of trehalose analogs that involves the use of intramolecular aglycone delivery for stereoselective formation of the 1,1-alpha,alpha-glycosidic bond. The glycosylation reaction afforded the desired isomer exclusively and in good yield.
• Automated Glycan Assembly of Complex Oligosaccharides Related to Blood Group Determinants
  作者：Heung Sik Hahm、Chien-Fu Liang、Chian-Hui Lai、Richard J. Fair、Frank Schuhmacher、Peter H. Seeberger

  DOI：10.1021/acs.joc.6b00554

  日期：2016.7.15

  Lactotetraosyl (Lc4) and neo-lactotetraosyl (nLc4) are backbones that are common to many glycans. Using automated glycan assembly, these common core structures were constructed and elaborated to access synthetically challenging glycans of biological relevance. The incorporation of alpha-fucoses is demonstrated for H-type I and II; alpha(1,3)-galactose epitopes were prepared, and the pentasaccharide HNK-1 required incorporation of a 3-O-sulfate. In addition to preparing the target structures, essential insights were gained regarding the relationships of glycosylating agents and nucleophiles as well as the linker stability.
• Prearranged Glycosides. Part 8. Intramolecular α-Galactosylation Via Succinoyl Tethered Glycosides
  作者：Thomas Ziegler、Ralf Dettmann、Ariffadhillah、Uwe Zettl

  DOI：10.1080/07328309908544056

  日期：1999.1

  Benzyl protected phenyl 1-thio-galactopyranoside donors which were tethered by a succinoyl linker at their positions 2 and 6, respectively, to position 3 of a blocked benzyl glucopyranoside acceptor with a 4-OH group solely afforded the corresponding alpha-(1-->4)-linked disaccharides upon intramolecular glycosylation. 4,6-Siloxane protected mannosides react with rearrangement of the siloxane group under similar conditions.
• Comparative solution and solid-phase glycosylations toward a disaccharide library
  作者：Károly Ágoston、Lars Kröger、Ágnes Ágoston、Gyula Dékány、Joachim Thiem

  DOI：10.1016/j.carres.2009.04.001

  日期：2009.8

  A comparative study on solution-phase and solid-phase oligosaccharide synthesis was performed. A 16-member library containing all regioisomers of Glc-Glc, Glc-Gal, Gal-Glc, and Gal-Gal disaccharides was synthesized both in solution and on solid phase. The various reaction conditions for different approaches and corresponding yields are analyzed and discussed. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of the trisaccharide portion of soyasaponin βg: evaluation of a new glucuronic acid acceptor
  作者：Karen Plé

  DOI：10.1016/s0008-6215(03)00195-2

  日期：2003.7

  The synthesis of the trisaccharide portion of soyasaponin betag was successfully achieved using a new glucuronic acid acceptor: methyl 1-O-allyl-3 4-di-O-methoxymethyl-beta-D-glucuronate (9). This compound and methyl 1-O-allyl-3,4-di-O-tert-butyldimethyl-silyl-beta-D-glucuronate (8) were both prepared from glucuronolactone via a glycal intermediate. The former compound 9 was successfully coupled to ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-beta-D-galactopyranoside (13) in excellent yield. Synthesis of the protected trisaccharide was then completed by the addition of a suitably protected rhamnose derivative to the disaccharide portion. The reactivity of the glucuronic acid derivative 9 was also explored with trichloroacetimidate and fluoride donors. (C) 2003 Elsevier Science Ltd. All rights reserved.